Sodium hydride → N-{6-[2-(5-Bromo-pyrimidin-2-yloxy)-ethoxy]-2-propyl-5-p-tolyl-pyrimidin-4-yl}-4-tert-butyl-benzenesulfonamide

HRID 2291

반응식

HRID 2291 반응식
[H-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([S:13]([NH:16][C:17]2[C:22]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)=[C:21]([O:30][CH2:31][CH2:32][OH:33])[N:20]=[C:19]([CH2:34][CH2:35][CH3:36])[N:18]=2)(=[O:15])=[O:14])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].Cl[C:38]1[N:43]=[CH:42][C:41]([Br:44])=[CH:40][N:39]=1>O1CCCC1.CC(N(C)C)=O>[C:3]([C:7]1[CH:8]=[CH:9][C:10]([S:13]([NH:16][C:17]2[C:22]([C:23]3[CH:24]=[CH:25][C:26]([CH3:29])=[CH:27][CH:28]=3)=[C:21]([O:30][CH2:31][CH2:32][O:33][C:38]3[N:43]=[CH:42][C:41]([Br:44])=[CH:40][N:39]=3)[N:20]=[C:19]([CH2:34][CH2:35][CH3:36])[N:18]=2)(=[O:14])=[O:15])=[CH:11][CH:12]=1)([CH3:5])([CH3:6])[CH3:4]

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 6066655-Bromo-2-chloropyrimidineHCID 196894984-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(4-methylphenyl)-2-n-propylpyrimidin-4-yl]benzenesulfonamide

생성물 1

HCID 19689505N-{6-[2-(5-Bromo-pyrimidin-2-yloxy)-ethoxy]-2-propyl-5-p-tolyl-pyrimidin-4-yl}-4-tert-butyl-benzenesulfonamide수율 91.4%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 31374Dimethylacetamide용매

실험 절차

To a suspension of sodium hydride (0.25 g) in tetrahydrofuran (5 ml) is added dropwise a solution of 4-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(4-methylphenyl)-2-n-propylpyrimidin-4-yl]benzenesulfonamide (1.00 g) in dimethylacetamide (3 ml) and tetrahydrofuran (10 ml) at room temperature, and thereto is added 2-chloro-5-bromopyrimidine (0.56 g), and the mixture is stirred at room temperature for 2.5 hours. The reaction mixture is acidified with ice-cold diluted hydrochloric acid, and extracted with ethyl acetate. The extract is washed, dried, and evaporated to remove the solvent. The resulting oily product is purified by silica gel column chromatography (solvent; chloroform), and crystallized from n-hexane to give 4-tert-butyl-N-[6-{2-(5-bromopyrimidin-2-yloxy)ethoxy}-5-(4-methylphenyl)-2-n-propylpyrimidin-4-yl]benzenesulfonamide (1.21 g) as crystals.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe extract is washed
  3. customdried
  4. customevaporated
  5. customto remove the solvent
  6. customThe resulting oily product is purified by silica gel column chromatography (solvent; chloroform)
  7. customcrystallized from n-hexane

출처 및 근거

ORD 기록
ord-f0bfe7cb12de4449ad46b88945212348
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728706

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